Hydrochloric Acid → HCID 71073924, compound

HRID 869682Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:12]2[CH:32]=[C:15]3[N:16]=[C:17]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH:18]=[C:19]([NH:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:14]3[N:13]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[ClH:33].O>C(O)C>[ClH:33].[CH3:1][C:2]1[C:3]([C:12]2[CH:32]=[C:15]3[N:16]=[C:17]([N:27]4[CH2:28][CH2:29][CH2:30][CH2:31]4)[CH:18]=[C:19]([NH:20][CH:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[N:14]3[N:13]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 2-(3-methylquinoxalin-2-yl)-5-pyrrolidin-1-yl-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (655 mg, 1.52 mmol) in ethanol (15 mL) was added 2N aqueous hydrochloric acid solution (0.915 mL). The mixture was heated at 80° C. for 3 h, and then water (3.1 mL) and ethanol (5.0 mL) was added. The mixture was clear solution and then cooled to ambient temperature to give 2-(3-methylquinoxalin-2-yl)-5-pyrrolidin-1-yl-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine hydrochloride (the compound of Example 1.001 listed in the Table of Examples as described hereinafter). 1H-NMR (500 MHz, DMSO-d6): δ 1.86-1.91 (4H, m), 2.04-2.06 (4H, m), 3.08 (3H, s), 3.46-3.53 (2H, m), 3.63 (4H, m), 3.94 (2H, m), 4.09 (1H, m), 5.62 (1H, s), 6.87 (1H, s), 7.83-7.90 (2H, m), 8.08 (1H, dd, J=8.2, 1.4 Hz), 8.14 (1H, dd, J=8.0, 1.3 Hz), 8.20 (1H, br).

Workup

temperaturecooled to ambient temperature

Sources & evidence

ORD record: ord-174ee087c57742b2a2a23e4ea0c7b550
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969376B2

Reaction notes

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